RK Hauler - have a similar dent - going up the ramp slow minimizes the bottoming out of my Ultra Classic.
We purchased ours in Nov of 08 and it has been a good trailer for us. Only problem I have now is that I purchased a 2011 Silverado and there is clearance issues with the pin box. I have raised the hitch and I will lower the pin box next of cut off a portion on the back of the pin box (about an inch). I have already made contact with my truck box once - filled the small dent with RTV and painted with touch up paint.
2009 Montana Mountaineer 347THT
TV - 2011 Chevy Silverado 3500HD LTZ CCLB LML SRW 4X4 Blue Granite Metallic